Thionyl Chloride → HCID 19907981, compound

Participants

Reaction Conditions

Reaction Steps

All four compounds were prepared by the same method. An example is presented below. 4-[2-(2-Allyloxyethoxy)ethoxy]benzyl alcohol (7.57 g, 0.03 mol) was dissolved in methylene chloride (100 mL), and SOCl2 (4.28 g, 0.036 mol) was added dropwise. After the addition was completed the reaction mixture was stirred at 40° C. for 1 hr. washed with water, 2% NaHCO3 aqueous solution, and water and dried over anhydrous MgSO4. The solvent was evaporated and the residual oil was purified by column chromatography (silica gel, a mixture of 1:3 ethyl acetate to n-hexane as eluent) to yield 6.52 g (80%) of a colorless oily product 14. 1H-NMR (CDCl3, TMS, δ in ppm): 3.55-4.19 (m, 10H, --CH2 --(O--CH2 --CH2)2), 4.55 (s, 2H, Ph--CH2 --), 5.23 and 5.78 (m, 3H, CH2 =CH--), 5.92 and 7.25 (2d, 4 aromatic protons).

Provenance & Evidence